Azo dye.



UNITED STATES PATENT oFFIcE.

LEOPOLD HES E AND OSCAR GUNTHER, OF ELBE'RFELD, AND ARTHUR ZARI, OFVOHWIN- 'IQEL, NEAR ELBERFELD, GERMANY, ASSIGNORS TO FARBENFABRIKENVORM. FRIEDR. BAYER (S: 00., OF ELBERFELD, GERMANY, A CORPORATION OFGERMANY.

AZO DYE.

No. 931,424. Specification of Letters Patent. Patented Aug. 17, 1909.Application filed April 8, 1909. Serial No. 488,699.

To ail whom it may concern: intermediate compound is precipitated by 55Be it known that we, LEOPOLD Hesse, the addition of hydrochloric acid,filtered of]? (lscAn GI'JNTHER, and ARTHUR ZART, doctors and transformedinto its sodium salt. This of philosophy, chemists, citizens of theGeris redissolved and rediazotized at-about 20 man Empire, residingat,respectively, Elber- C. The diazo compound. is then added to a feld,Elberfeld, and Vohwinkel, near Elbersolution of 365 parts of the sodiumsalt of 60 fold, Kingdom of Prussia, Germany, haveQ-benzoylamino-5-naphthol-7-sulfonic acid. invented new and usefulImprovements in ihe combination is completed by the addih'ew Azo Dyes,of which the following is :1 tion of sodium carbonate. specification.The dye is isolated in the usual way and This invention relates to themanufacture purified by resolution in Water. It is, after 5 c andproduction of new secondary disazo being dried and pulverized, in theshape of dyestuffs dyeing cotton from red to 'blue its sodium salt agreenish powder which is shades remarkable for their fastness to light.soluble in water with a red color and which They are obtained bycombining diazotized is soluble in concentrated sulfuric acid with I gaminoazo compounds of the naphthalene sea greenish-blue color. Byreduction with 70 I ries obtainable from naphthylamin comstannouschlorid and hydrochloric acid I pounds, especially naphthylamins, their5111- 2 naphthylamin eLS disulfonic acid, 2.5 I fonic acids,alpha-beta-, and beta-betaamidimethyLl.4-(liaminobenzene and2-benzoylnonaphthol sulfonic acids and suitable aminsamino-6-amino-5-naphthol-7-sulfonic acid 5 with acidylized derivativesof 2-a1nino-5- are obtained. The new dyestufi" dyes cotton 75 naphihol('UIHIJOIHMTS having the formula: dark red shades. The process iscarried out in an analo ous I I; 303B NHR way 011 starting from other ofthe above defined aminoazo compounds e. g. from those obtained fromalpha-naphthylamin2.5- or 0 i j I 3.6-disulfonic acid,beta-naphthylamin-1.6-

OH or 3.6-disulfonic acid, 1.5-aminonaphthol-7- I R meaning an acidradical, X meaning sulfonic acid, l.5-aminonaphthol-2.7-disulhydrogen orSO I-I)-. fonic acid, 2.5aminonaphthol-7-sulfonic acid I01'2.5-aminonaphthol-l.7-disulf0l1ic acid and I I The new dyestuffs arein the shape of their alkaline salts dark powders easily soluor on usingother amins as second comble in water. Upon reduction with stanponentsfor the production of the aminoazo nous chlorid and hydrochloric acidthe compounds, 6. g. meta-toluldin, anilin, cre- I 35 dyest-ufi's aredecomposed, a naphthylamin sidin, alpha-naphthylamin, alpha-naphthyl- Icompound, a diamin and an acidylized deamin-G-or 7-sulfon1c acld or onusing other i a 2.6-diamino-5-naphthol comend components, 6. g.2.-ethylurethane-- I napht-hol-7-sulfonic acid or l-7-disulfon1c acid,5.5-dioXy-7.7-disulfonic acid 2.2. di-

rivatn'e of pound having the formula:

. X 40 I I naphthylurea acetyl-2.5-aminonaphthol 7- so Yj Y sulfonicacid, 2-methyluret-hane-5-naphthol- M 7-sulf0nic acid,2-phenylurethane-5-naph- NH? I thol-7-sulfonic acid,2-phenylurea-5-naphthol-7-sulfon1c acid, meta-am1nobenzoyl-2.5- 45 areformed. They dissolve in concentrated aminonaphthol-7-sulfonic acid etc.

sulfuric acid With from a violet to green We claim: color.

I11 order to carry out this process we can obtainable by combining thediazo com a. g. proceed as follows, the parts being by pounds of thehereinbefore definedannno- 50 weight: 303 parts of Q-na hthylamin-tB-azo compounds with acldylized derlvatives disulfonic acid are diazotizedand the diazo of Q-amino-5-naphthol compounds of the l. The hereindescribed new azo dyestufi's I. i.

compound is then combined with 156.5 parts above given formula, whichdyestuffs are, of paraxylidin hydrochlorid in the usual after beln drledand pulverized, 1n the sodium acetate, the shape of tieir alkaline saltsdark powders way with the addition of Correction in Lettrs Patent No.931,424.

powder which is soluble in water with a red color and which is solublein concentrated sulfuric acid with a greenish-blue color; yielding uponreduction with stannous chlorid and hydrochloric acid Q-naphthylamin-4.8-disulfonic acid, 2.5-din1etl1yl-l.4-diamino benzene and 2benzoylamino 6 amino 5 naphthol-T-sulfonic acid; and dyeing cotton darkred shades, substantially as described.

In testimony whereof we have hereunto 25 set our hands in the presenceof two subscribing witnesses.

LEOPOLD HESSE. [n s.] OSCAR GUN THER. [1,. s.] ARTHUR ZART. [L. s.]

lVitnesses OTTO Kor'm, C. J. W .IGH'r.

It is hereby certified that in Letters Patent No. 931,424, grantedAugust 17 1909,

upon the application of Leopold Hesse and Oscar Gunther, of Elberfeld,and Arthur Zart, of Vohwinkel, near Elberfeld, Germany, for animprovement in Azo Dyes,

an error appears in the printed specification requiring correction asfollows: Page 2,

line 6, the numerals and Words 2.6-diamino-naphthol should read 2.6-ciiamz'no- 5-napltthol; and that the said Letters Patent should be readwith this correction therein that the same may conform to the record ofthe case in the Patent Oflice.

Signed and sealed this 5th day of October, A., D. 1909.

[SEAL.]

o. c. BILLINGS,

Acting Commissioner of Patents.

Correction in Lettrs Patent No. 931,424.

powder which is soluble in water with a red color and which is solublein concentrated sulfuric acid with a greenish-blue color; yielding uponreduction with stannous chlorid and hydrochloric acid Q-naphthylamin-4.8-disulfonic acid, 2.5-din1etl1yl-l.4-diamino benzene and 2benzoylamino 6 amino 5 naphthol-T-sulfonic acid; and dyeing cotton darkred shades, substantially as described.

In testimony whereof we have hereunto 25 set our hands in the presenceof two subscribing witnesses.

LEOPOLD HESSE. [n s.] OSCAR GUN THER. [1,. s.] ARTHUR ZART. [L. s.]

lVitnesses OTTO Kor'm, C. J. W .IGH'r.

It is hereby certified that in Letters Patent No. 931,424, grantedAugust 17 1909,

upon the application of Leopold Hesse and Oscar Gunther, of Elberfeld,and Arthur Zart, of Vohwinkel, near Elberfeld, Germany, for animprovement in Azo Dyes,

an error appears in the printed specification requiring correction asfollows: Page 2,

line 6, the numerals and Words 2.6-diamino-naphthol should read 2.6-ciiamz'no- 5-napltthol; and that the said Letters Patent should be readwith this correction therein that the same may conform to the record ofthe case in the Patent Oflice.

Signed and sealed this 5th day of October, A., D. 1909.

[SEAL.]

o. c. BILLINGS,

Acting Commissioner of Patents.

Correction in Letters Patent No. 931,424.

It is hereby certified that in Letters: Patent No. 931,424, grantedAugust 17, 1909. upon the application of Leopold Hesse and OscarGunther, of Elherfcld, and Arthur Zart, of Vohwinkel, near Elherfeld,Germany, for an improvement in A20 Dyes,"

an error appears in the printed specification requiring correction asfollows: Page 2, line 6, the numerals and words 2.H-dimninomaphtholshould read iifi a h'amv'nv- 5-naplatlwl; and that the said LettersPatent should he read with this correction therein that the same mayconform to the record of the case in the Patent Oflicc.

Signed and sealed this 5th day of ()ctohen A., D. 1909.

[SEAL] C. C. BILLINGS,

Acting Commissioner 0 Patents.

